Ai Sugiyama defeated Jennifer Capriati 5-7 6-2 6-2 in the San Diego round of 32 on hard. The upset overturned the form book — Jennifer Capriati came in leading the head-to-head 5–2. Ai Sugiyama narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-08-30 | US Open | R16 | hard | Jennifer Capriati | 7-5 6-2 |
| 2003-11-05 | WTA Tour Championships | RR | carpet | Jennifer Capriati | 7-5 7-6(3) |
| 2002-08-12 | Montreal | R16 | hard | Jennifer Capriati | 6-1 7-5 |
| 2002-08-04 | Los Angeles | QF | hard | Ai Sugiyama | 6-3 6-3 |
| 2000-01-17 | Australian Open | QF | hard | Jennifer Capriati | 6-0 6-2 |
| 1997-11-10 | Philadelphia | R32 | carpet | Ai Sugiyama | 6-1 6-2 |
| 1997-03-31 | Hilton Head | R32 | clay | Jennifer Capriati | 6-1 6-0 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (172 vs 31). ATP, WTA & Challenger.